5-Iodo-2-aminoindan (5-IAI): Chemistry, pharmacology, and toxicology of a research chemical producing MDMA-like effects

Coppola, Maurizio; Mondola, Raffaella

doi:10.1016/j.toxlet.2013.01.008

Cited by 17 publications

(21 citation statements)

References 54 publications

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“…5-IAI and MDAI substituted for MDMA in drug discrimination studies [20,34], but were considered less neurotoxic than MDMA [20,34,35]. This profile may increase the popularity of these aminoindanes [13]. The comparable monoamine transporter inhibition and release profile to MDMA [4,6] would predict that MDAI has very similar subjective effects to MDMA, and this is supported by user reports [12,36].…”

Section: Aminoindanesmentioning

confidence: 92%

“…In contrast to MDAI and MDMA [4,6], 5-IAI exhibited relevant binding to 5-HT receptors, including the 5-HT 2A receptor that is implicated in the action of hallucinogens [37]. 5-IAI is also considered a less potent MDMA substitute, but dysphoria, anxiety, and hallucinations have also been reported [13]. In contrast to the substituted aminoindanes, 2-AI selectively inhibited the NET, but not the DAT or SERT.…”

Section: Aminoindanesmentioning

confidence: 95%

“…The aim of the present study was to describe the effects on monoamine uptake and release of novel psychoactive substances that are not cathinones, but have been introduced into the illicit drug market as "legal highs" to typically mimic the subjective effects of MDMA or amphetamine-type stimulants. Aminoindanes, such as 5,6-methylenedioxy-2-aminoindane (MDAI) and 5-iodoaminoindane (5-IAI), became increasingly available over the Internet starting in 2010 as legal and, in the case of MDAI, allegedly less-neurotoxic alternatives to MDMA [11][12][13]. Piperazines have been used for more than a decade [14] and are commonly found in Ecstasy pills as substitutes for MDMA [15,16].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives

Simmler

Rickli

Schramm

et al. 2014

Biochemical Pharmacology

108

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Aminoindanes, piperazines, and pipradrol derivatives are novel psychoactive substances found in "Ecstasy" tablets as replacements for 3,4-methylenedioxymethamphetamine (MDMA) or substances sold as "ivory wave." The pharmacology of these MDMA-and methylphenidate-like substances is poorly known. We characterized the pharmacology of the aminoindanes 5,6-methylenedioxy-2-aminoindane (MDAI), 5-iodoaminoindane (5-IAI), and 2-aminoindane (2-AI), the piperazines meta-chlorophenylpiperazine (m-CPP), trifluoromethylphenylpiperazine (TFMPP), and 1-benzylpiperazine (BZP), and the BZP, D2PM, and 2-DPMP lacked serotonergic activity and TAAR 1 binding, in contrast to the aminoindanes and phenylpiperazines. In summary, all of the substances were monoamine transporter inhibitors, but marked differences were found in their 3 DAT vs. SERT inhibition profiles, release properties, and receptor interactions. The pharmacological profiles of D2PM and 2-DPMP likely predict a high abuse liability.

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Section: Aminoindanesmentioning

confidence: 92%

Section: Aminoindanesmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives

Simmler

Rickli

Schramm

et al. 2014

Biochemical Pharmacology

108

View full text Add to dashboard Cite

show abstract

“…In the experimental study [88] the dose 40 times as high than the dose causing behavioral changes had no toxic effects (including neurotoxic). And still, it does not mean that the substances are safe: the users were found to have hyperemia, serotonin syndrome, acute necrosis of skeletal muscles, and there were fatal cases [88][89][90]. Due to the fact that the number of active substance varies from one lot to another, it may be a problem of overdosage [92].…”

Section: Other New Psychoactive Substancesmentioning

confidence: 83%

“…Psychoactive substances of this group -MDAI (5,6-methylenedioxy-2-aminoindan), 5-IAI (5-iodo-2-aminoindan) and MMAI (5-methoxy-6-methyl-2-aminoindan) -have the so called entactogenic effect (i.e. they enhance the perception of self-emotions), and therefore, they are sold as "legal" MDMA substitutes [88]. These preparations are weak inhibitors of monoamine reuptake, and except this they stimulate nonvesicular serotonin release.…”

Section: Other New Psychoactive Substancesmentioning

confidence: 99%

Synthetic Cathinones and Cannabinoids Are New Psychoactive Substances (Review)

Larchenko¹,

Суворов²,

Andryukhin³

et al. 2017

Sovrem Tehnol Med

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New psychoactive substances, or designer drugs, are currently a large group of substances, primarily of synthetic origin, which are designed and come on a shadow market in circumvention of the current law. The popularity of these substances among young people is due to the off-the-shelf availability, low cost, and expected safety compared to traditional drugs. As practice shows, a resulting intoxication is life-threatening.Currently, the ordered data on these substances classes, as well as clinical manifestations of poisoning related to their consumption is practically non-existent due to certain difficulties in their diagnosis. The review considers the main groups of new psychoactive substances (synthetic cathinones and cannabinoids, derivatives of piperazine, aminoindans) circulating in a shadow market. We have distinguished the basic mechanisms of their effect on human body and described the main manifestations of their consumption.When writing the review we used the data of specialized poison control medical centers, as well as the information obtained from users.

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New psychoactive substances—Synthetic stimulants

Varı̀

Pichini

Giorgetti

et al. 2018

WIREs Forensic Science

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The expression "New Synthetic Stimulants" include classes of psychoactive compounds that share subjective effects in humans such as boosted mood or euphoria, feelings of empathy or compassion, increased sociability and sex drive, perceived increased ability to learn and focus, increased energy and alertness, with unpleasant outcomes like increased blood pressure and heart rate, paranoia or aberrations, decreased appetite, raised body temperature, clenched jaw or grinding teeth, dry mouth, insomnia, hallucinations, and aggressive or violent behavior. Synthetic stimulants act in the brain by increasing concentrations of neurotransmitters, mainly dopamine and serotonin. Dopamine is involved in attention, reward, and motivation whereas serotonin is involved in generating feelings of happiness and pleasure. Synthetic stimulants act on the two brain systems to different extents, accounting for their range of effects. Noradrenaline release is also stimulated by these compounds, but to a minor degree. In any case, long-term use of synthetic stimulants exhausts dopamine and serotonin systems in the brain. The nerve cells become desensitized to the drugs, which makes them resistant to the brain's own signaling molecules. This leads to tolerance and dependence, which can easily turn into addiction. Like classic stimulants (e.g., cocaine, methamphetamine), new synthetic stimulants can be highly addictive.

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5-Iodo-2-aminoindan (5-IAI): Chemistry, pharmacology, and toxicology of a research chemical producing MDMA-like effects

Cited by 17 publications

References 54 publications

Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives

Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives

Synthetic Cathinones and Cannabinoids Are New Psychoactive Substances (Review)

New psychoactive substances—Synthetic stimulants

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